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The star cornerback of his high school's football team, Van is kicked out of the house when his parents find out that he plans to marry his pregnant girlfriend Cheyenne. He moves in with Reba, his mother-in-law. During his final year of high school, Van supports his teenage wife during her pregnancy, is crowned Prom King, and continues to be a star on the football team. When Cheyenne goes into labor at their graduation, he carries her across the stage to grab both of their diplomas. Cheyenne gives birth that night to their daughter, Elizabeth.

After high school, Van goes to the University of Houston, after Reba convinces them to stay local for their child. Van and his family are supposed to move into on-campus housing as part of his football scholarship, but he loses the housing opportunity after his suspends his scholarship due to a knee injury. Van takes the semester off, and his family goes back to living with Reba. Throughout the second season, Van and his family worry about money to the point where they go on food stamps and Reba takes on a full-time job. Cheyenne and Reba frequently suggest Van reconcile with his wealthy parents, but it never works out because they do not approve of Cheyenne and treat Elizabeth the same as they did to Van growing up (showering them with expensive gifts instead of real care and affection as Reba does). Van eventually returns to playing football which makes Cheyenne feel lonely without him around as often.

Soon after returning to football, Van drops out of college because he has been recruited to the Arena Football League. Despite Reba's initial hesitance of him quitting his education, she comes to his side when she realizes how significant this step could help him get into the NFL. Finally, the Montgomery's have real money coming into their bank account which makes Cheyenne feel more secure about their future, but Van gets a little too happy with the cushion. He buys a sports car (which he names Rhonda) impulsively which causes tension between him and his wife until she relents to keeping the car as long as they agree to consult each other in the future about financial decisions. They come together later in the season when they decide to move out again, trying to go for an apartment that is out of their price range. The couple even goes so far as to forge Reba's signature, but their application is denied due to her poor credit. They continue living with Reba.

In the fourth season, Van gets traded to Denver and hires a sports agent to help negotiate his deal. The move infuriates Cheyenne who doesn't like his prolonged absence from their family life nor seeing his happiness in Denver without her there. Later, Van comes home with an injured tailbone, but the doctor reveals that he has spinal stenosis, a pre-existing condition that would have prevented Van from having a football career to begin with. Devastated and shocked, Van has to quit his football career and move back home. Initially, Van and his family fear the condition will also prevent him from getting paid for the rest of the year because the diagnosis is a pre-existing condition; however, his agent successfully gets him a $100K buy-out because the condition was not discovered during his initial team physical. Again, Van gets money-happy with his hefty paycheck. He buys his various family members appreciated but unnecessary gifts, including diamond earrings for his mother-in-law. Despite loving her dream-gift, Reba brings Van back down to reality, explaining that this paycheck is meant to be invested, not spent on extravagant gifts. Not knowing where to go after his football career, Van spends time doing various things such as fishing, helping Kyra with her band, playing online poker and showing Jake how to play football. All the while, his wife is busy going to school and taking care of their daughter, and eventually, she cracks, telling Van he needs to find a job.

After some convincing, Reba hires Van as her real estate assistant, but it turns out Van is a natural at selling houses. This causes tensions between Van and Reba who wishes she had Van's natural talent but also doesn't trust him to do the "hard" tasks. One morning while Reba is waking Van up, she finds an empty liquor bottle in his closet. She believes Van has a drinking problem, encourages him to seek help at alcoholic meetings and monitors him closely at home. It is later revealed that the bottle belonged to Cheyenne who is diagnosed as an alcoholic and ends up seeking help.

When Reba and Van finally come to turns as real estate partners, they agree to help Brock and Barbra Jean out of their financial hole by buying their house but letting them stay as tenants. Van takes pleasure in being a landlord despite it making Barbra Jean feel insecure (even going so far as to pay them in dimes).

His 5-year wedding anniversary approaches and he and Cheyenne agree it's a perfect time in their marriage to renew their vows. They plan a big wedding that is meant to be family and good friends, but Cheyenne is angered when she sees a lot of Van's business associates are in attendance after he dismisses inviting her support group friends. The couple gets into an argument at the ceremony with Cheyenne refuses to walk down the aisle, but everything is cut short when Reba collapses due to her high blood pressure. At the hospital, Reba forces Van and Cheyenne to talk over their issues. They know they are growing apart as both have new interests that are unique to them, but they agree to work it out because they still love each other.

In the sixth season, a prestigious real estate company offers Van a job that doesn't include Reba. Initially declining the job despite its good pay due to his loyalty to Reba, Van eventually accepts it with her blessing. It is later revealed that Cheyenne is pregnant with their second child, a son, and the young but growing family know it is time for them to move into their own home. They struggle with the idea of finally being on their own (as does Reba who is used to being close to them and watching over them), and they are even temporarily forced to move back in when Van accidentally sets a small fire while working on the heater. After coming to terms that they will be fine and it is time, Van and his family feel secure about being on their own, knowing Reba and the others will always be close by.

Van dated Cheyenne, the co-captain on the high school drill team, during high school, later getting her pregnant during their senior year. They get married, and Van moves in with his mother-in-law, Reba. While life for the young couple is rocky at times throughout their marriage, they keep pushing through because of their love for each other.

Kate was a business associate of Van's. After an innocent business meeting, Van had left his jacket in her car. She later returned it to Reba's house. When Cheyenne sees the jacket, she immediately suspects an affair, becoming infuriated with Van. At the airport, before he leaves to return to work, Cheyenne's parents force them to talk, and Cheyenne explains that she is afraid Van could cheat just as her father did to her mother. Van explains he would never be like her father, and Kate is nothing more than a business associate.

Van worked at Fat Tony's Pizzeria in the episode She Works Hard for their Money. He was originally "Cheese Captain" until Fat Tony's wife left him and he got promoted to delivery, but since he was working to afford half of the new car that Brock gave him and Cheyenne, he needed Reba to drive him.

Van played in the Arena Football League for the Houston ThunderBears until he was traded to the Colorado Crush and had to travel until he was diagnosed with Spinal Stenosis, a condition that prevented him from playing football.

While fixing the heater at his new house in Season 6, Van sets a small fire, causing his family to temporarily move back in with Reba.

He freaked out when he couldn't find Elizabeth during a game of hide-and-seek, demonstrating his potential overprotectiveness as a father in the future, particularly when she begins dating.

He is smarter than Barbra Jean.

He has a weak stomach as shown in the episode Ring-a-Ding when he arrives to Barbra Jean's family reunion and Brock asks him how he's feeling when he and Jake fought over a puke pail.

He is scared of small dogs, as mentioned in Who Killed Brock? because when he was a little kid his parents let him watch Cojo on TV, but it was on a nine-inch screen.

He is scared of spiders, claiming he's seen a huge man-eating spider.

He has a nervous bladder, when he and Cheyenne attempt to steal Reba's list, he constantly has to pee.

His favorite superhero is Underdog.

His poker screen name is screen name.

He would like Denzel Washington to play him in a movie.

His parents tried gifting him a brand new truck in order to buy back his love in Season 1, but Van returns it when he discovers they wanted nothing to do with his new family.

In the episode 'Thanksgiving' it is mentioned that they started their traditional football game his first year in the family when Jake was 2. This would make Van 12 when he became apart of the Hart family.

Ever since he was 6-years old he has never brushed his teeth other than Aquafresh.

It is revealed in the Pilot episode that he and Cheyenne lost their virginity to each other (which he is embarrassed to reveal to Reba and Brock).